Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C2H2Cl2O2 |
| Molecular Weight | 128.942 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C(Cl)Cl
InChI
InChIKey=JXTHNDFMNIQAHM-UHFFFAOYSA-N
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
| Molecular Formula | C2H2Cl2O2 |
| Molecular Weight | 128.942 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Dichloroacetic acid, often abbreviated DCA (dichloroacetate), is an acid analog of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA are used as drugs since they inhibit the enzyme pyruvate dehydrogenase kinase. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. A phase 1 study in 5 patients concluded that DCA was safe, but wasn't designed to establish effectiveness.
DCA was approved for use in Canada in 1989 (as a topical formulation for the treatment of warts and for cauterization and removal of a wide variety of skin and tissue lesions), but was cancelled post market. DCA is a noncompetitive inhibitor of the endoplasmic reticulum enzyme HMG CoA reductase, which catalyzes the rate limiting step in cholesterol biosynthesis. DCA has been researched in adults, children, animals, and cells as a monotherapy as well as in
combination with other therapies for the treatment of severe metabolic disorders including diabetes and hypercholesterolemia, lactic acidosis, certain heart conditions, and cancer. DCA has been prescribed to reduce tumour size and tumour markers, prevent angiogenesis, reduce
cancer related symptoms, manage pain, and aid in palliation.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.2 mM [Ki] | |||
Target ID: CHEMBL4766 |
1.0 mM [Ki] | ||
Target ID: CHEMBL3893 |
8.0 mM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mammalian cell cytotoxicity and genotoxicity analysis of drinking water disinfection by-products. | 2002 |
|
| Genetic polymorphisms in assessing interindividual variability in delivered dose. | 2002 Apr |
|
| An acetyl group deficit limits mitochondrial ATP production at the onset of exercise. | 2002 Apr |
|
| [Drug therapy for mitochondrial diseases]. | 2002 Apr |
|
| New large solar photocatalytic plant: set-up and preliminary results. | 2002 Apr |
|
| Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine. | 2002 Aug |
|
| Low-dose pharmacokinetics and oral bioavailability of dichloroacetate in naive and GST-zeta-depleted rats. | 2002 Aug |
|
| Dichloroacetate stimulates glycogen accumulation in primary hepatocytes through an insulin-independent mechanism. | 2002 Aug |
|
| Metabolic regulation of collagen I in fibroblasts isolated from normal peritoneum and adhesions by dichloroacetic acid. | 2002 Dec |
|
| Nephrotoxicity of chlorofluoroacetic acid in rats. | 2002 Dec |
|
| Degradation pathways of trichloroethylene and 1,1,1-trichloroethane by Mycobacterium sp. TA27. | 2002 Feb |
|
| Dichloroacetate therapy in Leigh syndrome with a mitochondrial T8993C mutation. | 2002 Jul |
|
| Solar photodegradation of dichloroacetic acid and 2,4-dichlorophenol using an enhanced photo-Fenton process. | 2002 Jul |
|
| Kinetics of the biotransformation of maleylacetone and chlorofluoroacetic acid by polymorphic variants of human glutathione transferase zeta (hGSTZ1-1). | 2002 Jul |
|
| Manipulations in glycogen metabolism and the failure to influence infarct size in the ischaemic rabbit heart. | 2002 Jul |
|
| Bromochloroacetic acid exerts qualitative effects on rat sperm: implications for a novel biomarker. | 2002 Jul |
|
| Skeletal muscle metabolism is unaffected by DCA infusion and hyperoxia after onset of intense aerobic exercise. | 2002 Jul |
|
| Contribution of dichloroacetate and trichloroacetate to liver tumor induction in mice by trichloroethylene. | 2002 Jul 1 |
|
| Immunohistochemical localization and activity of glutathione transferase zeta (GSTZ1-1) in rat tissues. | 2002 Jun |
|
| Glutathione and K(+) channel remodeling in postinfarction rat heart. | 2002 Jun |
|
| Alkylation and inactivation of human glutathione transferase zeta (hGSTZ1-1) by maleylacetone and fumarylacetone. | 2002 May |
|
| Distribution of haloacetic acids in the water columns of the Laurentian Great Lakes and Lake Malawi. | 2002 May 1 |
|
| Dichloroacetate toxicokinetics and disruption of tyrosine catabolism in B6C3F1 mice: dose-response relationships and age as a modifying factor. | 2002 May 1 |
|
| The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure. | 2002 Nov |
|
| Mass spectral characterization of dichloroacetic acid-modified human glutathione transferase zeta. | 2002 Nov |
|
| Stearoyl-CoA desaturase 1 (Scd1) gene overexpression is associated with genetic predisposition to hepatocarcinogenesis in mice and rats. | 2002 Nov |
|
| Brief increase in carbohydrate oxidation after reperfusion reverses myocardial stunning in conscious pigs. | 2002 Nov 26 |
|
| [Acute complications due to diabetes mellitus: Lactic acidosis]. | 2002 Oct |
|
| The acetyl group deficit at the onset of contraction in ischaemic canine skeletal muscle. | 2002 Oct 15 |
|
| Time-resolved optical Kerr-effect spectroscopy of low-frequency dynamics in Di-L-alanine, poly-L-alanine, and lysozyme in solution. | 2002 Oct 16 |
|
| Is lactate a mediator of hypoxia-induced anapyrexia? | 2002 Sep |
|
| Chloroacetic acids in European soils and vegetation. | 2003 Apr |
|
| Population kinetics, efficacy, and safety of dichloroacetate for lactic acidosis due to severe malaria in children. | 2003 Apr |
|
| Measurement of 13C/12C of chloroacetic acids by gas chromatography/combustion/isotope ratio mass spectrometry. | 2003 Feb |
|
| Dichloroacetate accelerates the fall in intracellular PO2 at onset of contractions in Xenopus single muscle fibers. | 2003 Feb |
|
| [Adverse effects of dichloroacetate in a girl with mitochondrial disorder]. | 2003 Jan |
|
| A 2-year dose-response study of lesion sequences during hepatocellular carcinogenesis in the male B6C3F(1) mouse given the drinking water chemical dichloroacetic acid. | 2003 Jan |
|
| Synthesis and immunogenic properties of phosphopeptides related to the human insulin receptor. | 2003 Jan |
|
| Differential modulation of glucose, lactate, and pyruvate oxidation by insulin and dichloroacetate in the rat heart. | 2003 Jul |
|
| Formation of chloroacetic acids from soil, humic acid and phenolic moieties. | 2003 Jul |
|
| Perturbation of maleylacetoacetic acid metabolism in rats with dichloroacetic Acid-induced glutathione transferase zeta deficiency. | 2003 Jul |
|
| Altered gene expression in mouse livers after dichloroacetic acid exposure. | 2003 Mar |
|
| Physicochemical characterization of phosphinic pseudopeptides by capillary zone electrophoresis in highly acidic background electrolytes. | 2003 Mar |
|
| Pyruvate-dependent preconditioning and cardioprotection in murine myocardium. | 2003 Mar |
|
| Identification of trichloroethylene and its metabolites in human seminal fluid of workers exposed to trichloroethylene. | 2003 Mar |
|
| Regulation of transforming growth factor-beta, type III collagen, and fibronectin by dichloroacetic acid in human fibroblasts from normal peritoneum and adhesions. | 2003 May |
|
| Field level evaluation and risk assessment of the toxicity of dichloroacetic acid to the aquatic macrophytes Lemna gibba, Myriophyllum spicatum, and Myriophyllum sibiricum. | 2003 May |
|
| Differential effect of DCA treatment on the pyruvate dehydrogenase complex in patients with severe PDHC deficiency. | 2003 May |
|
| Dichloroacetate increases skeletal muscle pyruvate dehydrogenase activity during acute limb ischemia. | 2003 May-Jun |
|
| Effects of dichloroacetate on VO2 and intramuscular 31P metabolite kinetics during high-intensity exercise in humans. | 2003 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Patients are typically started at a lower dose and slowly increased until the benefit is observed or
adverse effects become apparent. Doses are based upon weight, and optimal therapeutic dosing is
typically achieved at a range of 50 mg/kg to 80 mg/kg. In order to avoid adverse effects such as
peripheral neuropathy, intravenous DCA is administered twice weekly and oral DCA is given in a
cyclical nature with two weeks of administration being followed by a week-long break from
treatment. http://www.oicc.ca/uploads/dca-health-professional.pdf
Brain Cancer treatment: Oral DCA given twice daily for the 24 week period of the study.
Route of Administration:
Oral
Cells were treated with 25 and 50 mmol/L dichloroacetate
for 24 hours, and cell-cycle profiles were analyzed using
flow cytometry. Dichloroacetate treatment induced changes in the
cell-cycle profiles of all tested glioblastoma cells.
Specifically, after 24 hours of treatment with 25 mmol/L dichloroacetate, there was a slight increase (not significant) in the
cells in G2–M phase in U87 and U251 cells and a 1.2-fold increase
(P < 0.001) in RN1 cells. Significant increase in the mean
percentage of all 3 tested cell lines in G2–M phase was observed
when dichloroacetate dose was increased to 50 mmol/L.
When compared with untreated control (U251, 8.8%; U87,
15.2%; RN1, 14.1%), dichloroacetate treatment increased the
proportion of cells at G2–M phase to 35.5%, 34.7%, and
45.5%, respectively
| Substance Class |
Chemical
Created
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| Record UNII |
9LSH52S3LQ
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Validated (UNII)
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